Job Overview
Location
Chicago, IL, United States of America
Job Type
Full-time
Category
Account Executive
Date Posted
February 26, 2026
Full Job Description
đź“‹ Description
- • As a Territory Account Executive at Block, Inc. in Chicago, you will be the driving force behind our mission to empower local businesses through our comprehensive suite of commerce and financial services solutions. This is a high-impact, field-driven role where you will spend approximately 80% of your time actively engaging with businesses in your assigned territory. Your primary objective will be to build and nurture relationships with sellers, understand their unique challenges, and demonstrate how Square's integrated ecosystem can help them grow, operate more efficiently, and thrive in today's competitive market.
- • You will be responsible for the entire sales cycle, from prospecting and lead generation to closing deals and ensuring a seamless handover for new customers. This requires a proactive, self-starter mentality and the ability to operate independently in a fast-paced, dynamic environment. Your day-to-day will involve extensive face-to-face interactions, conducting live product demonstrations, and building a robust sales pipeline from the ground up.
- • A key aspect of this role is becoming the recognized Square expert within your community. This means being a consistent, reliable, and value-driven presence for local businesses. You'll leverage your deep understanding of Square's offerings—spanning point-of-sale hardware, software solutions for online sales, inventory management, appointment booking, payroll, and financial services like business loans and buy-now-pay-later options—to address specific merchant needs.
- • You will develop a disciplined, repeatable engine for generating new business opportunities. This includes a strong focus on door-to-door outreach, active participation in community events, strategic networking, and cultivating high-value partnerships with local organizations and channel partners. The goal is to create a consistent stream of qualified leads and referrals that fuel your territory's growth.
- • Mastering key industry verticals such as restaurants, retail, and service-based businesses is crucial. You will need to develop deep expertise in the operational nuances and challenges faced by businesses in these sectors. This knowledge will enable you to diagnose pain points accurately and position the most effective Square solutions, selling consultatively and competitively to meet and exceed client expectations.
- • Success in this role hinges on exceptional execution and a high degree of accountability. You will be expected to maintain rigorous operational discipline, meticulously tracking your activities, managing your sales pipeline, and providing accurate forecasts within Salesforce. Continuous performance measurement and a commitment to ongoing improvement are essential.
- • You will consistently strive to exceed sales quotas, operating within a culture that upholds high standards and rewards high performance. Your ability to strategically navigate the market, build trust, and deliver tangible value will be the keys to your success and the growth of the businesses you serve.
- • This role offers a unique opportunity to make a significant impact on the economic empowerment of small and medium-sized businesses in Chicago. By bringing Square's innovative solutions directly to merchants, you will play a vital role in helping them scale, compete, and achieve their full potential. If you are driven by meaningful work, possess a strong sales acumen, and thrive in a challenging, results-oriented environment, this position is an ideal fit for your career aspirations.
- • You will be instrumental in elevating Square's brand visibility and establishing strong, trust-based relationships with local sellers. Your presence in the market will serve as a competitive advantage, showcasing our commitment to supporting businesses at every stage of their growth journey. You will also collaborate closely with internal teams to ensure a seamless onboarding experience for new clients, accelerating their time-to-value and fostering long-term partnerships.
- • Implementing a disciplined referral strategy will be a key tactic, transforming satisfied customers into advocates and sources of future business. This proactive approach to customer engagement and network building is fundamental to sustainable territory growth and market penetration.
- • Your ability to sell consultatively means going beyond simply presenting features; it involves understanding the client's business objectives, identifying potential roadblocks, and architecting a solution that directly addresses their needs and drives measurable results. This consultative approach, combined with a competitive edge, ensures that Square remains the preferred partner for businesses seeking to optimize their operations and expand their reach.
- • Maintaining accurate and up-to-date records in Salesforce is non-negotiable. This data provides critical insights into market trends, sales performance, and forecasting accuracy, enabling data-driven decision-making and continuous refinement of sales strategies. Your commitment to operational excellence will directly contribute to the overall success of the sales team and the company.
- • Ultimately, you will be a key player in building a best-in-class field sales organization, contributing to Square's continued expansion and its mission to empower sellers worldwide. This role demands resilience, strategic thinking, and an unwavering focus on achieving exceptional results.
🎯 Requirements
- • Full language proficiency in both English and Spanish.
- • 3+ years of sales experience in a full cycle closing role with field sales experience.
- • Proven track record of exceeding sales targets and closing complex deals.
- • Ability to drive deals independently in a fast-paced, dynamic environment.
- • Reliable transportation and residency within the market you are serving.
🏖️ Benefits
- • Competitive salary with variable compensation (target annual earnings range: $123,400 - $223,100 depending on zone).
- • Comprehensive medical insurance.
- • Flexible time off and modern family planning benefits.
- • Retirement savings plans.
- • Opportunities for professional development and career growth within a leading technology company.
Skills & Technologies
Remote
$148k-223k
Degree Required
About Block, Inc.
Block, Inc. builds financial technology and commerce tools for businesses and consumers. Its ecosystem spans Square point-of-sale systems, Cash App peer-to-peer payments, Afterpay buy-now-pay-later services, and Bitcoin-focused initiatives including TBD and hardware wallets. Operating globally, the company offers integrated hardware, software, and banking solutions that enable sellers to accept payments, manage inventory, obtain loans, and sell online, while giving individuals access to digital banking, stock investing, and cryptocurrency services.
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